CN101641111B - Formulations containing cynara scolymus and phaseolus vulgaris extracts which are useful in the treatment of obesity - Google Patents
Formulations containing cynara scolymus and phaseolus vulgaris extracts which are useful in the treatment of obesity Download PDFInfo
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- CN101641111B CN101641111B CN200880007206XA CN200880007206A CN101641111B CN 101641111 B CN101641111 B CN 101641111B CN 200880007206X A CN200880007206X A CN 200880007206XA CN 200880007206 A CN200880007206 A CN 200880007206A CN 101641111 B CN101641111 B CN 101641111B
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- cynara scolymus
- semen phaseoli
- cyhara cardunculus
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- 239000000284 extract Substances 0.000 title claims abstract description 68
- 244000019459 Cynara cardunculus Species 0.000 title claims abstract description 31
- 235000019106 Cynara scolymus Nutrition 0.000 title claims abstract description 31
- 239000000203 mixture Substances 0.000 title claims abstract description 22
- 244000046052 Phaseolus vulgaris Species 0.000 title abstract description 7
- 208000008589 Obesity Diseases 0.000 title abstract description 5
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- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
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- YDDUMTOHNYZQPO-RVXRWRFUSA-N Cynarine Chemical compound O([C@@H]1C[C@@](C[C@H]([C@@H]1O)O)(OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C(O)=O)C(=O)\C=C\C1=CC=C(O)C(O)=C1 YDDUMTOHNYZQPO-RVXRWRFUSA-N 0.000 description 2
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- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
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- AMTWCFIAVKBGOD-UHFFFAOYSA-N dioxosilane;methoxy-dimethyl-trimethylsilyloxysilane Chemical compound O=[Si]=O.CO[Si](C)(C)O[Si](C)(C)C AMTWCFIAVKBGOD-UHFFFAOYSA-N 0.000 description 2
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Botany (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Medical Informatics (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Abstract
The present invention relates to a Cynara scolymus extract with a high content of caffeoylquinic acids, and a composition containing said Cynara scolymus extract with a Phaseolus vulgaris extract. Said composition is useful in reducing obesity as it reduces cholesterol, triglycerides and blood glucose by sensitising the cells to insulin. This combination, when taken before meals, reduces the appetite, leading to a reduction in body weight. The extracts are preferably formulated in Oenothera biennis oil, fish oil, or oils rich in unsaturated Omega-3 fatty acids.
Description
Invention field
The present invention relates to comprise the preparation of Cynara scolymus L (Cyhara cardunculus.) (Cynara Scolymus) extract (preferably having high-load caffeotannic acid) and Kidney bean (Phaseolus vulgaris) extract, its ratio is 1: 0.25 to 1: 1.
Said composition is used for reducing fat, because its cholesterol reducing, triglyceride, blood glucose and appetite.
Background of invention
Obesity is one of current important health problem, and particularly in industrialized country, it has aspect the heart circulation serious consequence with the skeleton aspect.
Carbohydrate is the important source of heat, and the lipogenesis in the individuality with type ii diabetes of promoting to be liable to obesity.Because hyperglycemia causes energy storage to increase, so it is extremely important to reduce the availability of material of biological available glucose.Because starch is the main source of glucose, so the perhaps synthetic specific alpha-glucosidase and the alpha-amylase inhibitor that from plant material, obtain are studied.For a long time, people have known that some seed and sarcocarp (pulses) contain such material, and it is just edible before not boiling fully, may produce ill effect.Many sarcocarp contain protease inhibitor, amylase inhibitor and stop the eater to continue edible their material through reducing appetite.These materials are called as phytohemagglutinin, under high dose, can cause the pancreas hypertrophy, but than being used to control appetite under the low dosage.
Under high dose, these phytohemagglutinin have been avoided the transhipment of intestinal and have been combined enterocyte, and they cause the secretion of cholecystokinin at this, and cholecystokinin is a kind of stimulating pancreas secretion and the trophic hormone that causes its expansion then.Cholecystokinin also has favourable effect, because it can reduce appetite through reducing the stomach motion.
Known from document, water extract of Cynara scolymus L (Cyhara cardunculus.) or aqueous alcohol extract have the activity that reduces cholesterolemia, promotes bile secretion and dyspepsia.The activity of this reduction cholesterolemia has been in the news for many years, and it is relevant with two types of materials: cinarine, a kind of dicaffeoylquinic acid; With the flavone compound derived from luteolin, it has been proved at the cholesterol of vitro inhibition liver synthetic.Part is active relevant with the specific choleretic effect of Cynara scolymus L (Cyhara cardunculus.) extract.The method for distilling of Cynara scolymus L (Cyhara cardunculus.) is described in WO2007/006391.
Invention is described
Have now found that with Cynara scolymus L (Cyhara cardunculus.) extract and Semen Phaseoli Vulgaris extract combination, can obtain surprising slimming effect, this effect is proportional with the dosage of being used; The effect that tables of data phaneroplasm in rat heavily alleviates is not relevant with the blood sugar lowering level simply, and relevant with the clearly reduction of food consumption.Various pharmacological experiments prove: even the not absorption of erstricted diet, the reduction of this food intake is also irrelevant with simple poisonous effect, but relevant with change feed desire.
The combination of the material of Carlina acaulis extract (it helps strengthen the removing of fat and glucose through the glucose transport in change intestinal and the liver) and reduction starch metabolism is being kept body weight and is being stoped particular importance in the weight increase.
Detailed Description Of The Invention
Available extract according to the present invention is commercial Carlina acaulis extract, according to the extract of WO2007/006391 or have high-load caffeotannic acid and the Carlina acaulis extract of luteolin glucosides, described last a kind of extract extracts with the mixture of C1-C3 alcohol or itself and water from undried edible fresh idea (heads) and obtains.
Ethanol or ethanol/water mixture are preferably used in the extraction of from undried edible Cynara scolymus L (Cyhara cardunculus.) fresh idea, carrying out, and especially use 7: the ethanol/water of 3v/v ratio.Behind purification, the extract of acquisition is different from known extract owing to its high-load caffeotannic acid with the flavonoid that the luteolin glucosides is represented.This extract also has hypoglycemic activity.This extract can be from multiple Cynara scolymus L (Cyhara cardunculus.) kind, preferred thorn-like mutation (spiny variety), even preparation in the more preferably Sadinia thorn-like mutation (Sardinian spinyvariety).
The caffeotannic acid amount that preferred Cynara scolymus L (Cyhara cardunculus.) extract contains is 30-60%, and is preferred about 45%, and the content of the flavonoid of representing with the luteolin glucosides is 2-5%, preferred about 2.5%.
But the extract of Semen Phaseoli Vulgaris extract commodity in useization; But, preferably at the Semen Phaseoli Vulgaris extract described in the PCT/EP2006/012012.Said extract is that the mixture with the second alcohol and water extracts acquisition from Kidney bean (Phaseolus sp.); It is characterized in that alpha-amylase inhibitor content is that 1200-1600USP/mg (the HPLC titre is 7-14%w/w) and phytohemagglutinin content are 12; 000-30,000HAU/g.Said extract can obtain through following method, and this method comprises:
A) extract Kidney bean with the aqueous buffer solution of pH value 3-6.5, separation and Extraction thing from Biomass subsequently, it can further extract with buffer, till AMS and phytohemagglutinin inhibitor have extracted;
B) with the extract filtration that merges or centrifugal, be concentrated into volume corresponding to the weight about 10% of the initial extract Biomass after centrifugal;
C) spissated water extract is carried out differential precipitation with Diluted Alcohol, to final concentration be 60-70%v/v;
D) sediment separate out is perhaps used interception 10 with 60% ethanol redeposition from demineralised water, the film of 000Da carries out diafiltration, and it is dry to precipitate residue.
Ratio is the combination of two kinds of extracts of 1: 0.25 to 1: 1; Comprise that every dosage is that Cynara scolymus L (Cyhara cardunculus.) extract and the every dosage of 50-500mg, preferred 200mg is the Semen Phaseoli Vulgaris extract of 50-200mg, preferred 100mg, taking medicine before meal with or take when being rich in the food of carbohydrate edible.
The hypoglycemic activity of the present composition is superior to two kinds of hypoglycemic activities that composition is independent separately surprisingly.According to people such as Tormo MA, Br.J.Nutr.96, the resulting result of method of 539,2006 narrations is presented in the following table.
The Cynara scolymus L (Cyhara cardunculus.) extract of table-purification, Semen Phaseoli Vulgaris extract and their combination give the influence of Wistar rat blood sugar of the food of limit amount to the mode with restriction feed 1 hour every day
| The Cynara scolymus L (Cyhara cardunculus.) extract mg/kg of purification is oral | Semen Phaseoli Vulgaris extract mg/kg is oral | The AUC of plasma glucose levels (mg/dL) |
| 0 | 0 | 30800±950 |
| 50 | 0 | 25100±700＊(-18％) |
| 0 | 50 | 27700±600(-10％) |
| 25 | 25 | 19800±800＊＊(-36％) |
Every treated animal number: 8
*P＜0.05
*P＜0.01 is with respect to contrast
Compositions of the present invention is suitable for mixing in the pharmaceutical preparation, said preparation such as tablet, dragee, soft hard gelatin capsule and cellulose capsule.This extract is preferably prepared in the oil that is rich in polyunsaturated ω 3/ ω 6 acids, for example Radix Oenotherae erythrosepalae (Oenothera biennis) (Radix Oenotherae erythrosepalae) oil.
In the mankind with every day 50-1000mg dosage confirmed and viewed identical result in laboratory animal.
Following embodiment is used for the present invention is done detailed explanation.
Embodiment 1-prepares the extract of Cynara scolymus L (Cyhara cardunculus.) thorn-like mutation (Cynara scolymus vr.Spinosus)
The fresh idea that 2kg is shredded with refrigerated Cynara scolymus L (Cyhara cardunculus.) Sadinia thorn-like mutation (Cynara scolymusvr.Sardinian Spinosus) when gathering in the crops is loaded in the percolation filter that has heating jacket; 95 ° of EtOH with 4760ml cover, to obtain about 70% pure content (supposing that water content is 85% in this plant).Under 70 ℃, kept in touch 3 hours, and unloaded sample subsequently.In successive extraction, extract 70 ℃ of following cover plants with the EtOH of 70%v/v, be 3 hours minimum time of contact.Carry out 5 extractions altogether, use the solvent of about 15L.
Merge percolate and, obtain about 15% dried residue at 35 ℃ of following vacuum concentration.
Make it cooling at ambient temperature, separate insoluble part, clarifying aqueous solution is loaded in the pillar that is filled with 530ml XAD-7HP resin.
The washing pillar, earlier with the water washing (removing eluent) of 530ml, 90% EtOH with 1325ml washs subsequently.Aqueous ethanol elution is concentrated, 50 ℃ of following vacuum dryings 24 hours.Obtain the extract of 18.59g purification.HPLC titre: caffeotannic acid 49.13%, flavonoid 2.68%.
Embodiment 2-is mixed with the oily suspension that is used for Perle with Cynara scolymus L (Cyhara cardunculus.) and Semen Phaseoli Vulgaris extract
Unit composition:
Cynara scolymus L (Cyhara cardunculus.) extract 100mg
Semen Phaseoli Vulgaris extract 100mg
Glyceryl monostearate 30mg
Soybean lecithin 10mg
Radix Oenotherae erythrosepalae oil is in right amount to reach 700mg
Method for preparing
Extremely about 70 ℃ of-heating Radix Oenotherae erythrosepalae oil, and under agitation glyceryl monostearate is melted in oil.
-soybean lecithin is added in the solution of gained.
-extract of Cynara scolymus L (Cyhara cardunculus.) and Kidney bean is dispersed in the gained solution, guarantee its uniform distribution.
-when keeping stirring, make the solution cooling of gained gradually.
Embodiment 3-is formulated in Cynara scolymus L (Cyhara cardunculus.) and Semen Phaseoli Vulgaris extract in the hard gelatin capsule
Unit composition:
Cynara scolymus L (Cyhara cardunculus.) extract 150mg
Semen Phaseoli Vulgaris extract 50mg
Microcrystalline Cellulose 200mg
Lactose 95mg
Silicon dioxide 5mg
Method for preparing
-extract, microcrystalline Cellulose, lactose and silicon dioxide are mixed.
-install to the mixture branch that obtains in the hard gelatin capsule.
Embodiment 4-is formulated in Cynara scolymus L (Cyhara cardunculus.) and Semen Phaseoli Vulgaris extract in the sustained-release granular formulation
Unit composition
Cynara scolymus L (Cyhara cardunculus.) extract 100mg
Semen Phaseoli Vulgaris extract 50mg
Microcrystalline Cellulose 100mg
Polyvidone 10mg
Sodium carboxymethyl cellulose 8mg
EUDRAGIT S100 50mg
Triethyl citrate 3.2mg
Pulvis Talci 8mg
Simethicone 0.3mg
Method for preparing:
-with the aqueous solution of polyvidone extract, microcrystalline Cellulose and sodium carboxymethyl cellulose are granulated.
-with the particle drying and the demarcation of gained.
-with the aqueous suspension of EUDRAGIT S100, triethyl citrate, Pulvis Talci and Simethicone granule is carried out coating.
Embodiment 5-is formulated in Cynara scolymus L (Cyhara cardunculus.) and Semen Phaseoli Vulgaris extract in the immediate-release granules agent
Unit composition:
Cynara scolymus L (Cyhara cardunculus.) extract 100mg
Semen Phaseoli Vulgaris extract 50mg
Microcrystalline Cellulose 100mg
Polyvidone 10mg
Sodium carboxymethyl cellulose 8mg
Method for preparing:
-with the aqueous solution of polyvidone extract, microcrystalline Cellulose and sodium carboxymethyl cellulose are granulated.
-with the particle drying and the demarcation of gained.
Embodiment 6-has the Cynara scolymus L (Cyhara cardunculus.) of different release characteristics and the granulate mixture of Semen Phaseoli Vulgaris extract
Method for preparing:
-embodiment 4 described the granules with 50% mix with 50% embodiment 5 described granules mutually.
-the mixture branch of gained is installed in the hard gelatin capsule.
Claims (3)
1. comprising ratio is 1: 0.25 to 1: 1 the Cynara scolymus L (Cyhara cardunculus.) extract and the compositions of Semen Phaseoli Vulgaris extract; Wherein the caffeotannic acid content that has of Cynara scolymus L (Cyhara cardunculus.) extract is 30-60%; Luteolin glucosides content is 2-5%; Wherein Semen Phaseoli Vulgaris extract is characterised in that alpha-amylase inhibitor content is that 1200-1600USP/mg and phytohemagglutinin content are 12,000-30,000HAU/g.
2. compositions as claimed in claim 1, it also contains Radix Oenotherae erythrosepalae oil.
3. has the purposes in the medicine of blood sugar lowering and anti-obesic action like the compositions of claim 1-2 described in each in preparation.
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| US90532007P | 2007-03-07 | 2007-03-07 | |
| EP07425132A EP1967198B1 (en) | 2007-03-07 | 2007-03-07 | Formulations containing cynara scolymus and phaseolus vulgaris extracts which are useful in the treatment of obesity |
| US60/905,320 | 2007-03-07 | ||
| EP07425132.3 | 2007-03-07 | ||
| PCT/EP2008/001787 WO2008107184A1 (en) | 2007-03-07 | 2008-03-06 | Formulations containing cynara scolymus and phaseolus vulgaris extracts which are useful in the treatment of obesity |
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| CN101641111B true CN101641111B (en) | 2012-05-23 |
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| EP (1) | EP1967198B1 (en) |
| JP (1) | JP5355424B2 (en) |
| KR (1) | KR101456555B1 (en) |
| CN (1) | CN101641111B (en) |
| AT (1) | ATE431155T1 (en) |
| AU (1) | AU2008224057B2 (en) |
| BR (1) | BRPI0808563B1 (en) |
| CA (1) | CA2680078C (en) |
| DE (1) | DE602007001128D1 (en) |
| DK (1) | DK1967198T3 (en) |
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| HK (1) | HK1121694A1 (en) |
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| NO (1) | NO339322B1 (en) |
| PL (1) | PL1967198T3 (en) |
| PT (1) | PT1967198E (en) |
| RU (1) | RU2453323C2 (en) |
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| ITMI20052450A1 (en) | 2005-12-22 | 2007-06-23 | Indena Spa | PHASEOLUS VULGARIS EXTRACTS THEIR USE AND FORMULATIONS THAT CONTAIN THEM |
| CN101874822A (en) | 2009-04-27 | 2010-11-03 | 玫琳凯有限公司 | Botanical anti-acne formulations |
| EP2345646A1 (en) * | 2010-01-14 | 2011-07-20 | InterMed Discovery GmbH | Use of tricyclic sesquiterpene lactones in the treatment of obesity and related diseases and non-therapeutic treatable conditions |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| KR101330190B1 (en) | 2011-09-20 | 2013-11-15 | (주)그린솔루션스 | Cosmetic composition for inhibits adipogenesis of Prunella vulgaris extract via modulated HO-1 expression |
| KR102245069B1 (en) | 2011-12-19 | 2021-04-26 | 마리 케이 인코포레이티드 | Combination of plant extrats to improve skin tone |
| ITMI20121570A1 (en) * | 2012-09-20 | 2014-03-21 | Indena Spa | NEW EXTRACTS OF CYNARA SCOLIMUS, COFFEA SPP. AND EUROPEAN OLEA FOR THE TREATMENT OF METABOLIC SYNDROME |
| ITMI20121727A1 (en) * | 2012-10-12 | 2014-04-13 | Indena Spa | FORMULATIONS FOR TREATMENT AND PREVENTION OF OBESITY |
| ITMI20121749A1 (en) * | 2012-10-16 | 2014-04-17 | Indena Spa | HELIANTHUS ANNUUS EXTRACTS USEFUL IN THE TREATMENT OF THE METABOLIC SYNDROME AND IN THE DECREASE OF THE GLICEMIC FOOD INDEX AND PROCEDURE FOR THEIR PREPARATION AND THE COMPOSITIONS THAT CONTAIN THEM |
| KR102323049B1 (en) | 2014-03-10 | 2021-11-05 | 마리 케이 인코포레이티드 | Skin lightening compositions |
| DE202014005450U1 (en) * | 2014-07-04 | 2015-10-06 | Ursapharm Arzneimittel Gmbh | Lactose-free medicine |
| US20160302451A1 (en) * | 2015-04-16 | 2016-10-20 | Michael Hudnall | Medical Food for Patients with Chronic Liver Disease |
| FR3075570B1 (en) * | 2017-12-22 | 2020-01-03 | Agro Innovation International | STIMULATION OF NITRIFICATION OF A SOIL WITH COMPOSITIONS COMPRISING A PLANT EXTRACT |
| IT201900000367A1 (en) * | 2019-01-10 | 2020-07-10 | Altergon Sa | COMPOSITIONS INCLUDING A PEPTIDE ABLE TO STIMULATE THE GPRC6A-DEPENDENT SIGNAL PATH |
| CN110433280A (en) * | 2019-09-11 | 2019-11-12 | 周口师范学院 | Application of the phytohemagglutin phytolectin in preparation prevention or treatment antiobesity agents |
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| GB8524275D0 (en) * | 1985-10-02 | 1985-11-06 | Efamol Ltd | Pharmaceutical & dietary compositions |
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| Publication number | Publication date |
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| US20080220097A1 (en) | 2008-09-11 |
| WO2008107184A1 (en) | 2008-09-12 |
| AU2008224057B2 (en) | 2012-07-19 |
| PT1967198E (en) | 2009-06-15 |
| NO339322B1 (en) | 2016-11-28 |
| EP1967198A1 (en) | 2008-09-10 |
| EP1967198B1 (en) | 2009-05-13 |
| US20100136145A1 (en) | 2010-06-03 |
| DK1967198T3 (en) | 2009-08-10 |
| IL200709A (en) | 2013-07-31 |
| JP5355424B2 (en) | 2013-11-27 |
| RU2009133338A (en) | 2011-03-10 |
| US7887854B2 (en) | 2011-02-15 |
| RU2453323C2 (en) | 2012-06-20 |
| DE602007001128D1 (en) | 2009-06-25 |
| CN101641111A (en) | 2010-02-03 |
| KR20090118051A (en) | 2009-11-17 |
| JP2010520246A (en) | 2010-06-10 |
| US7887855B2 (en) | 2011-02-15 |
| HK1121694A1 (en) | 2009-04-30 |
| KR101456555B1 (en) | 2014-10-31 |
| BRPI0808563A2 (en) | 2014-09-02 |
| PL1967198T3 (en) | 2009-10-30 |
| ES2323815T3 (en) | 2009-07-24 |
| IL200709A0 (en) | 2010-05-17 |
| CA2680078A1 (en) | 2008-09-12 |
| BRPI0808563B1 (en) | 2018-02-14 |
| SI1967198T1 (en) | 2009-08-31 |
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| ATE431155T1 (en) | 2009-05-15 |
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| CA2680078C (en) | 2016-12-06 |
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